PL129368B1 - Process for preparing 2-alkyl-2-p-chlorophenylacetonitrile - Google Patents
Process for preparing 2-alkyl-2-p-chlorophenylacetonitrile Download PDFInfo
- Publication number
- PL129368B1 PL129368B1 PL1981232390A PL23239081A PL129368B1 PL 129368 B1 PL129368 B1 PL 129368B1 PL 1981232390 A PL1981232390 A PL 1981232390A PL 23239081 A PL23239081 A PL 23239081A PL 129368 B1 PL129368 B1 PL 129368B1
- Authority
- PL
- Poland
- Prior art keywords
- lower alkyl
- methyl
- group
- butyl
- valeryl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 isovaleryl Chemical group 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims description 8
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 abstract description 2
- 239000000642 acaricide Substances 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- GIZHRKQXPROIGC-UHFFFAOYSA-N 2-(4-chlorophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(Cl)C=C1 GIZHRKQXPROIGC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GTIKLPYCSAMPNG-UHFFFAOYSA-N 2-(3-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(CC#N)=C1 GTIKLPYCSAMPNG-UHFFFAOYSA-N 0.000 description 1
- RBGSZIRWNWQDOK-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(Cl)C=C1 RBGSZIRWNWQDOK-UHFFFAOYSA-N 0.000 description 1
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17279080A | 1980-07-28 | 1980-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL232390A1 PL232390A1 (enrdf_load_stackoverflow) | 1982-02-15 |
| PL129368B1 true PL129368B1 (en) | 1984-05-31 |
Family
ID=22629252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981232390A PL129368B1 (en) | 1980-07-28 | 1981-07-28 | Process for preparing 2-alkyl-2-p-chlorophenylacetonitrile |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100598271B1 (ko) * | 1999-12-20 | 2006-07-07 | 에스케이 주식회사 | 3-(1-시아노알킬)벤조산의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5325538A (en) * | 1976-08-23 | 1978-03-09 | Sumitomo Chem Co Ltd | Preparation of 3-methyl-2-(4-halogenophenyl)butyronitril |
-
1981
- 1981-07-08 DK DK301981A patent/DK301981A/da not_active Application Discontinuation
- 1981-07-24 JP JP56115417A patent/JPS5753450A/ja active Pending
- 1981-07-24 CS CS815676A patent/CS226031B2/cs unknown
- 1981-07-24 KR KR1019810002692A patent/KR830006190A/ko not_active Ceased
- 1981-07-27 IL IL63427A patent/IL63427A/xx unknown
- 1981-07-27 DD DD81232127A patent/DD201674A5/de unknown
- 1981-07-27 AT AT81105930T patent/ATE8043T1/de not_active IP Right Cessation
- 1981-07-27 EP EP81105930A patent/EP0045088B1/en not_active Expired
- 1981-07-27 ZA ZA815132A patent/ZA815132B/xx unknown
- 1981-07-27 BR BR8104832A patent/BR8104832A/pt unknown
- 1981-07-27 DE DE8181105930T patent/DE3164308D1/de not_active Expired
- 1981-07-28 PL PL1981232390A patent/PL129368B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL63427A (en) | 1985-02-28 |
| ZA815132B (en) | 1982-10-27 |
| JPS5753450A (en) | 1982-03-30 |
| PL232390A1 (enrdf_load_stackoverflow) | 1982-02-15 |
| DE3164308D1 (en) | 1984-07-26 |
| EP0045088B1 (en) | 1984-06-20 |
| KR830006190A (ko) | 1983-09-20 |
| EP0045088A1 (en) | 1982-02-03 |
| IL63427A0 (en) | 1981-10-30 |
| BR8104832A (pt) | 1982-04-13 |
| CS226031B2 (en) | 1984-03-19 |
| DK301981A (da) | 1982-01-29 |
| ATE8043T1 (de) | 1984-07-15 |
| DD201674A5 (de) | 1983-08-03 |
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